Head of Cyber and Cloud Technology

Senior Director of Information Technology Father Bill's & MainSpring is committed to ending and preventing homelessness in Southern Massachusetts with programs that provide emergency and permanent housing and help people obtain skills, jobs, housing, and services. We help people who are struggling with homelessness or are at risk of homelessness to achieve self-sufficiency. Father Bill's & MainSpring is a growing and dynamic social service agency with expertise in emergency and permanent housing, job training and placement, and prevention services for individuals and families in need. Over the next five years, our strategic focus includes an increase in affordable, permanent supportive housing, a more efficient model of care for families experiencing homelessness, commitment to an enhanced delivery model to reduce the need for shelter, and improved community relations in order to achieve these goals. Our staff are thoughtful and caring individuals who share our passion for these ideals and creative approaches to helping people improve their lives.

We offer
a generous benefits package and a comprehensive orientation and training program, as well as ample opportunities for advancement for qualified individuals who show a commitment to our Mission. We are seeking candidates for either full-time or fractional engagement. Any annual salary listed applies to the full-time position only and does not apply to fractional work. The Senior Director of Information Technology provides senior-level leadership, strategic direction, and operational oversight for all IT systems and services across Father Bill's & MainSpring. This role is responsible for developing and executing a multi-year IT roadmap that aligns technology investments with organizational priorities, ensuring that IT is a core driver of efficiency, security, and service delivery. This position oversees internal IT staff, managed service providers, and consulting partners, ensuring cohesive, high-quality service delivery across all locations. This role also maintains responsibility for the overall safety, security, and integrity of the organization's IT systems, data, and infrastructure. This position leads to major areas including IT strategy, systems implementation, infrastructure and operations, cybersecurity and compliance, AI and innovation strategy, vendor/consultant management, and IT project portfolio oversight. It also has a longstanding commitment to strategic planning and evaluation of its performance outcomes and trends. A commitment to ensuring that compliance, program fidelity, and contract management are an essential role for all leadership positions. A commitment to strategic planning, intentional growth, and program development. Strategic IT Leadership Develop and maintain a comprehensive multi-year IT strategic roadmap, aligning technology with FBMS priorities including housing, operations, compliance, and staff support. Lead organizational decision-making regarding in-house vs. outsourced IT services, ensuring the most effective and scalable delivery model. Establish IT governance practices, including prioritization frameworks, project intake processes, and performance metrics. Proactively guide leadership on technology investments and risks. IT Security, Risk, and System Safety Oversee the overall safety and security of all IT systems, including networks, devices, cloud environments, and user access. Ensure implementation and monitoring of key security controls such as access management, encryption, endpoint protection, and compliance standards. Lead development of incident response, disaster recovery, and business continuity plans, including data backup and restoration processes. Ensure staff training on cybersecurity awareness and safe use of technology. Management of IT Staff, MSP, and Consulting Partners Provide leadership and supervision to internal IT staff, fostering a strong, service-oriented team of culture. Oversee all managed service providers (MSPs), ensuring effective ticketing, troubleshooting, escalation, and network management support. Manage relationships with consulting agencies, ensuring alignment with project goals, timelines, and deliverables. Serve as the central point of coordination across internal teams, MSPs, and consulting partners. IT Operations & Service Delivery Ensure effective day-to-day IT operations including: Helpdesk and troubleshooting services Device and asset lifecycle management Microsoft 365 and core systems administration Provide hands-on leadership in critical implementations, issue resolution, and staff training when needed. IT Project Portfolio & Implementation Leadership Oversee a portfolio of IT projects, including enterprise system implementations, infrastructure upgrades, and cybersecurity initiatives. Ensure projects are well-scoped, resourced, and aligned with organizational priorities. Lead